
Vacation rentals with a pool in Kailua-Kona
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Kailua-Kona
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

HAVEN: Poolside Sanctuary with Heavenly Views
HAVEN Where the changing colors of the heavens melt into the sea. This is a place where dreams are born and special moments of your life unfold. Tranquility, privacy, and stunning beauty await you. A masterclass of design in harmony with nature, this exquisite and inspired home beckons you; a salve for body and soul. Whether you are submerged in the saltwater pool or lounging inside one your deluxe bedroom suites, the views will enchant you, providing an ever-changing patina of color & light.

Spectacular View, Direct Oceanfront Kona,Top Floor
ALOHA, WE INVITE YOU TO RELAX AT SEA VILLAGE Our lovely top floor condo is perfect for you! Sit back and take in the spectacular view from the lanai as you watch dolphins and whales (in season) during the day and beautiful sunsets in the evening! Lose yourself in the never ending sound of waves throughout the condo. Enjoy a closet full of essentials for visiting gorgeous beaches on the island. Downtown Kailua-Kona is a short mile walk from the condo, or relax at the oceanfront pool and hot tub!

Peaceful Paradise
Experience ALOHA in this spacious, ocean view gem providing a place of delight and relaxation. 2 miles to downtown Kona. Comfortable, clean, sun-kissed and welcoming - perfect for unwinding after a day of island sight-seeing. The charming, stylish space has a private entrance and is located on the ground floor of a large two-story home. You will experience all the comforts of home including an ohana kitchen, living area, bbq, and lovely, large outdoor lanai. Our goal is to give 5 star stays

Aloha Paradise! Remodeled with A/C & Ocean View!
Best unit at Kailua-Kona’s popular Sea Village and one of the only with A/C! Captivating ocean views, breezes, tropical sights and sounds greet you in this easily accessible ground floor unit. Start your day on the private lanai watching the spinner dolphins and end it with a glass of wine watching sunset over the ocean. This fully updated, turn-key condo boasts open concept living and is 5 minutes to downtown. An ideal base for an individual, couple or small families to explore the Big Island!

Longboard Studio at Kona Magic Sands Beach
Welcome to LongBoard Studio – Kona’s premier direct oceanfront escape at Magic Sands Beach! This stylish, film-featured studio offers stunning ocean views, a brand-new lanai with teak furniture, and full-width NanaWall doors for seamless indoor-outdoor living. Enjoy a gourmet kitchen, AC, queen bed, in-unit laundry, and the sound of waves at your doorstep. Perfect for relaxing, writing, or watching dolphins & whales from your lanai. Steps to the beach, serenity, and aloha! TA-005-037-8752-01

Ocean Views~by Honl's Beach~Heart of Kona~AC
ENJOY OCEAN VIEWS from a newly renovated Stylish condo in one of Kona's most desirable locations. Condo is an apx 6 to 8 min walk to a variety of Ocean Side Restaurants, entertainment and a quick walk to Honl's Beach. No rental car is needed as you are a short walk into town. The condo looks directly out to the Pacific Ocean and is on the ground floor so (no long stairs to climb). Free dedicated parking spot, which is so IMPORTANT in KONA now! 65" SMART TV, AC, the SOFA folds to a 2nd bed.

Updated condo with ocean views & air conditioning
Kick back and relax at this renovated condo with partial ocean views, an oceanfront saltwater pool, and lusciously landscaped grounds. This air-conditioned unit boasts a central location just 1.3 miles from the heart of downtown Kona. Conveniently located between downtown Kona and the world-famous Magic Sands beach, this is the perfect home base to explore everything Hawaii Island has to offer. Enjoy the shared BBQs and private sandy beach area as you soak up Kona's sensational sunsets.

Suite Magic Sands Beach
Save money & time! Ho'omalu located just off of Alii drive "Ironman Route" is only an 11 minute walk to magic sands beach and many more hot spots. In a private and tranquil gated community this modern day Villa awaits where sophistication meets relaxed Hawaiian living. The inviting pool enveloped with mature tropical landscaping is the centerpiece to this compound and features upscale finishes and flooring. The apartment is on the second level. Ask about our car rental fleet discounts.

Downtown Kona Plaza Condo w/AC
Visit all the Big Island has to offer and lay your head to rest at this comfortable, renovated condo located in the heart of downtown Kona. Situated on historical Ali'i Drive, we are just steps from shops, restaurants, coffee houses, and beaches. Take in the breathtaking sunsets and hear the nightly luau from the enclosed lanai. Enjoy the newly refinished pool, and head up to the sunset deck for a bbq or cocktail. Catch charters, sunset cruises, and snorkel tours off of Kailua Pier.

Poolside Studio🤙🏻Ocean View / AC / King🛌10min➡️Beach
A gorgeous remodeled studio featuring an ocean view lanai with a pool right outside. The lanai has a huge umbrella and bbq, and is a fully enclosed dining area with a self-closing gate to keep your kids safely away from the pool. The interior is all freshly renovated in 2020 with stylish and comfortable furniture. Covered parking is steps from the entry and plenty of quality beach gear is available for you to use anytime. Ice-cold A/C and Apple TV make relaxing inside just as nice.

1-Bedroom Suite with Private Pool and Garden Lanai
🌬AC included in price! ☀️We invite you to stay with us at our peaceful 1-bedroom studio `ohana unit in the heart of Kailua-Kona, Hawai`i. We offer a private bathroom, kitchenette, and coffee station to fulfill your traveling and exploring needs. 💦Or stay in and hang out poolside by your own private pool that comes with a comfy seating area, lounge chairs, and a grill. 🌿Whatever you choose, we hope to create a relaxing environment for you to unwind and feel at home.

On-the-Ocean; Stunning Corner Unit, Spacious, A/C!
Right-on-the-ocean, newly renovated, upscale and spacious condo in a gated boutique complex. Unbelievable views from the lanai and living room. Top floor corner unit with windows everywhere so you feel like you are living outside. King bed and queen sleeper sofa with memory foam mattress for up to 4 guests. Ocean-front pool with community BBQ. Quiet; set back from Ali'i Drive. Close to everything--just one mile from downtown Kona. Reserved parking spot. AC.
Popular amenities for Kailua-Kona rentals with a pool
House rentals with a pool

Mollie’s Paradise Resort Home - No Cleaning Fee!

Private Pool - 180° Ocean View - Minutes to Beach

Tropical Oasis Home with Pool and Steps to Beach

Tiny House Hawaii

Huge Kona Home • Ocean View • Pool • 4 bdrms • AC

Panoramic Ocean Views With Private Saltwater Pool

Big Family Home, Pool, Views, Yard, Lanai, Clean!

Ocean, Sunset, Mountain & Celestial Views
Condo rentals with a pool

Oceanfront Condo/Hawaiian Style. 1Bd, w/AC & Wifi

Inna's Downtown-Walk to Beach and to Supermarket!

Keauhou Garden - Ocean view - Walk to Harbor

2 Bedroom Penthouse Condo With Ocean View And Pool

Charming Condo in the Heart of Kona, Pool & A/C

Kailua Kona Downtown Condo Walk to Pier & Beaches

Honua Studio *Ocean Views on the Golf Course!

Studio condo, King bed, pool view on Alii Drive
Other vacation rentals with a pool

WAVES! WAVES! ON THE OCEAN! BOUTIQUE COMPLEX

Centrally Located Downtown Kona Condo

Luxury couple’s retreat w ocean view/AC/king bed

Brand NEW Oceanfront Retreat! Steps to Beach!

Hawai'i paradise at Kona Isle

Stunning Oceanfront Beach Condo!

NEW! ADORABLEbungalow in Kona

Oceanfront Chic • Just Renovated
When is the best time to visit Kailua-Kona?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 213 | € 228 | € 206 | € 200 | € 186 | € 188 | € 194 | € 189 | € 179 | € 200 | € 189 | € 204 |
| Avg. temp | 6°C | 6°C | 6°C | 7°C | 9°C | 10°C | 9°C | 9°C | 9°C | 9°C | 7°C | 6°C |
Quick stats about vacation rentals with a pool in Kailua-Kona

Total vacation rentals
Explore 1,940 vacation rentals in Kailua-Kona

Nightly prices starting at
Kailua-Kona vacation rentals start at € 43 per night before taxes and fees

Verified guest reviews
Over 73,110 verified reviews to help you choose

Family-friendly vacation rentals
970 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 50 rentals that welcome pets

Rentals with dedicated workspaces
1,050 properties have a dedicated workspace

Wi-Fi availability
1,920 of Kailua-Kona vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Kailua-Kona rentals

4.8 Average rating
Kailua-Kona stays are highly rated by guests—averaging 4.8 out of 5!
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- Hapuna Beach
- Pahoa Beach
- Kaunaoa Beach
- Mauna Kea Golf Course
- Kohanaiki Private Club Community
- Ke‘EI Beach
- Waikōloa Beach
- Mauna Lani Golf
- Volcano Golf and Country Club
- 49 Black Sand Beach
- Waikoloa Beach Golf Course
- Kuki’o Golf & Beach Club
- Kona Dog Beach
- Hapuna Golf Course
- Makalawena Beach
- Kona Country Club
- Nanea Golf Club
- Kealakekua Bay State Historical Park
- Mauumae Beach
- ʻAlula Beach
- Honokohau Beach
- Pololū Beach
- Mahaiʻula Beach
- Wawaloli Beach
- Things to do Kailua-Kona
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